Anthrimide-carbazole dyestuffs



UNITED STATE$ TENT GEE-ICE 2,473,949 ANTHRIMIDE CARBAZOLE DYESTUFFS 1 Hermann Hauser, Binningen, and Max Bommer,

Riehen, Switzerland, assignors-to the Swiss firm of Cilia Limited No Drawing: Original application April 20, 1943, Serial N 0. 483,804. Divided and this application Section 1, Public Law 690, August 8, 1946 Patent expires April 18, 1962 1 Claim. (Cl. 260-316) This is a division of our co-pending applicawherein one X stands for a benzoylamino group tion Serial No. 483,804, filed April 20, 1943 (now and the other X for hydrogen. U. S. Patent No. 2,459,424, granted January 18, The products of the invention are valuable vat 1949 dyestuffs. They can be used for example for The present invention is concerned with new 5 dyeing and printing vegetable fibers fast violetanthroquinone dyestufis and more particularly brown tints. those of the anthrimide type, i. e. of that type The following examples illustrate the invention, of dyestuffs in which anthraquinone radicals the parts being by weight unless otherwise are interconnected with other radicals by means stated: of imino groups. The said other radicals may Ema I also be anthraquinone radicals, or may be of mm 8 1 another type preferably aromatic The present 39.6 parts of 1:4-dichloro-S-benzoylaminoaninvention is also concerned with dyestuifs of the thraquinone (1 mol), 223 parts of Laminoam so-called anthrimide-carbazole type. Anthrithmqumone (1 mol) and 343 parts of amino mide-carbazoles are usually obtained by treating 4 benzoylaminoanthraquinone (1 mol) are tanthrimides with conde s ng agents Such as ed to boiling for 18 hours, together with 2 parts aluminium ch o ide 0 m Pases Sulfuric of cuprous chloride, 25 parts of sodium carbonate acid and its functional derivatives, such as and 400 parts of naphthalene t about 130 Q chlorosulfonlc acid- 800 parts of chlorobenzene are added and the Further obJects of the present invention be- 20 product f the reactlon filt r d off at 5 55 C a l:4-diha1ogen-5-benzoylaminoanthraquinone, pound which pr obably corresponds with the for example 1:4-dibromo or 1:4-dichloro-5-benformula;

portion of l-aminoanthraquinone and one molecular proportion of l-amino--benzoylaminoan- NH NH-Q thraquinone and carbazolizing the trianthrimide 0: =0 thus obtained. The condensation may be effect- I ed by heating the components in boiling naphthalene with addition of an acid binding agent as a copper salt. The carbazolizing reaction may be efiected by means of alum nium chloride, preferably in combination with tertiary aromatic compounds such as pyridine. The resulting compounds correspond to the formula or is a mixture of both, dissolves in concentrated sulphuric acid to an olive solution. On adding this solution to Water, olive flocks are obtained.

Example 2 To a mixture of parts of pyridine and parts of aluminium chloride prepared at -100 0., 20 parts of the trianthrimide obtained as described in Example 1 are added at C. in several portions, and the whole heated for 1 hour to -135" C. The melted mass is then added to dilute caustic soda and the pyridine distilled 05 in steam. The dyestuff is then isolated from the distillation residue by filtration, whereas the aluminium goes into the filtrate in the form of sodium aluminate.

The new dyestufif dissolves to a grass-green solution in concentrated sulphuric acid. It dyes cotton from the vat a very fast and very strong 15 violet-brown shade.

Having thus described the invention, what is claimed is:

4 An anthrimide-carbazole of the formula wherein one X stands for a benzoylamino group and the other X for hydrogen.

HERMANN HAUSER. MAX BOMMER.

No references cited. 

